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首页> 外文期刊>Chemistry: A European journal >N-Heterocyclic Olefins as Electron Donors in Combination with Triarylborane Acceptors: Synthesis, Optical and Electronic Properties of D-π-A Compounds
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N-Heterocyclic Olefins as Electron Donors in Combination with Triarylborane Acceptors: Synthesis, Optical and Electronic Properties of D-π-A Compounds

机译：作为电子给体的N-杂环烯烃与三芳基亚硼烷受体组合：D-π-的合成，光学和电子性质 - 一种化合物

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摘要

N-heterocyclic olefins (NHOs), relatives of N-heterocyclic carbenes (NHCs), exhibit high nucleophilicity and soft Lewis basic character. To investigate their p-electron donating ability, NHOs were attached to triarylborane p-acceptors (A) giving donor (D)-π-A compounds 1-3. In addition, an enamine p-donor analogue (4) was synthesized for comparison. UV-visible absorption studies show a larger red shift for the NHO-containing boranes than for the enamine analogue, a relative of cyclic (alkyl)(amino) carbenes (CAACs). Solvent-dependent emission studies indicate that 1-4 have moderate intramolecular charge-transfer (ICT) behavior. Electrochemical investigations reveal that the NHO-containing boranes have extremely low reversible oxidation potentials (e.g., for 3, E_(1/2)~(ox)=-0.40 V vs. ferrocene/ferrocenium, Fc/Fc~+, in THF). Time-dependent (TD) DFT calculations show that the HOMOs of 1-3 are much more destabilized than that of the enamine-containing 4, which confirms the stronger donating ability of NHOs.
机译：N-杂环烯烃（NHOS），N-杂环碳酸盐（NHC）的亲属，表现出高亲核和软刘易斯碱性特征。为了研究其P型电子捐赠能力，将NHOS连接到三芳基硼烷P受体（A）上，给予供体（D）-II-α-A化合物1-3。另外，合成了烯氨氨酸p-助剂类似物（4）以进行比较。紫外线可见吸收研究显示含NHO硼烷的较大的红移，而不是烯氨基类似物，环状（烷基）（氨基）碳酸盐（CAAC）的相对的硼烷。依赖于溶剂依赖性排放研究表明1-4具有中度分子内电荷转移（ICT）行为。电化学研究表明，含NHO的硼烷具有极低的可逆氧化电位（例如，对于3，E_（1/2）〜（牛）= - 0.40V与二茂铁/二茂铁，FC / FC〜+，THF） 。时间依赖性（TD）DFT计算表明，1-3的HOMOS比含烯胺的4的HOMOS更稳定，这证实了NHOS的更强的捐献能力。

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  • 来源
    《Chemistry: A European journal》 |2019年第60期|共8页
  • 作者

    Jiang He; Florian Rauch; Alexandra Friedrich; Daniel Sieh; Tatjana Ribbeck; Ivo Krummenacher; Holger Braunschweig; Maik Finze; Todd B. Marder;

  • 作者单位

    Institute for Inorganic Chemistry and Institute for Sustainable Chemistry &

    Catalysis with Boron (ICB) Julius-Maximilians-Universit?t Werzburg Am Hubland 97074 Werzburg (Germany);

    Institute for Inorganic Chemistry and Institute for Sustainable Chemistry &

    Catalysis with Boron (ICB) Julius-Maximilians-Universit?t Werzburg Am Hubland 97074 Werzburg (Germany);

    Institute for Inorganic Chemistry and Institute for Sustainable Chemistry &

    Catalysis with Boron (ICB) Julius-Maximilians-Universit?t Werzburg Am Hubland 97074 Werzburg (Germany);

    Institute for Inorganic Chemistry and Institute for Sustainable Chemistry &

    Catalysis with Boron (ICB) Julius-Maximilians-Universit?t Werzburg Am Hubland 97074 Werzburg (Germany);

    Institute for Inorganic Chemistry and Institute for Sustainable Chemistry &

    Catalysis with Boron (ICB) Julius-Maximilians-Universit?t Werzburg Am Hubland 97074 Werzburg (Germany);

    Institute for Inorganic Chemistry and Institute for Sustainable Chemistry &

    Catalysis with Boron (ICB) Julius-Maximilians-Universit?t Werzburg Am Hubland 97074 Werzburg (Germany);

    Institute for Inorganic Chemistry and Institute for Sustainable Chemistry &

    Catalysis with Boron (ICB) Julius-Maximilians-Universit?t Werzburg Am Hubland 97074 Werzburg (Germany);

    Institute for Inorganic Chemistry and Institute for Sustainable Chemistry &

    Catalysis with Boron (ICB) Julius-Maximilians-Universit?t Werzburg Am Hubland 97074 Werzburg (Germany);

    Institute for Inorganic Chemistry and Institute for Sustainable Chemistry &

    Catalysis with Boron (ICB) Julius-Maximilians-Universit?t Werzburg Am Hubland 97074 Werzburg (Germany);

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 应用化学;
  • 关键词

    donor-acceptor systems; electrochemistry; Nheterocyclic olefins; photophysical properties; triarylboranes;

    机译：供体 - 受体系统;电化学;Nhetercyclic烯烃;光药性;三芳纶硼烷;

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